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Nuances in fundamental Suzuki−Miyaura cross-couplings employing [Pd(PPh3)4]: poor reactivity of aryl Iodides at lower temperatures

Citation

Ho, CC and Olding, A and Smith, JA and Bissember, AC, Nuances in fundamental Suzuki−Miyaura cross-couplings employing [Pd(PPh3)4]: poor reactivity of aryl Iodides at lower temperatures, Organometallics, 37, (11) pp. 1745-1750. ISSN 0276-7333 (2018) [Refereed Article]


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DOI: doi:10.1021/acs.organomet.8b00189

Abstract

We have explored fundamental Pd-catalyzed Csp2− Csp2 Suzuki−Miyaura cross-couplings of aryl iodides (Ar−I) employing "classical" Pd/PPh3 catalyst systems. Surprisingly, we observed particularly inefficient couplings of these ostensibly reactive electrophiles in a range of conventional solvent mixtures at lower temperatures (∼50 °C), which was in stark contrast to analogous reactions featuring the equivalent aryl bromides. This feature of well-established Pd/PPh3-mediated Suzuki−Miyaura reactions has received scant attention in the literature. Most significantly, our studies suggest that the inefficient coupling of aryl iodides at lower temperatures derives from the unexpectedly poor turnover of the key on-cycle intermediate trans-[Pd(PPh3) 2(Ar)(I)] (or related PdII−I species) in the presence of PPh3.

Item Details

Item Type:Refereed Article
Keywords:Suzuki–Miyaura, palladium cross-coupling, aryl iodides
Research Division:Chemical Sciences
Research Group:Inorganic Chemistry
Research Field:Transition Metal Chemistry
Objective Division:Expanding Knowledge
Objective Group:Expanding Knowledge
Objective Field:Expanding Knowledge in the Chemical Sciences
Author:Ho, CC (Dr Curtis Ho)
Author:Olding, A (Mr Angus Olding)
Author:Smith, JA (Associate Professor Jason Smith)
Author:Bissember, AC (Dr Alex Bissember)
ID Code:126418
Year Published:2018
Deposited By:Chemistry
Deposited On:2018-06-12
Last Modified:2018-06-13
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